Diurethanes and herbicidal compositions containing the same

ABSTRACT

A composition containing at least one compound of the formula ##STR1## in which R is alkyl, alkenyl, alkinyl, halogenoalkyl or alkoxyalkyl, 
     R 1  is alkoxyalkyl or dialkoxyalkyl, 
     R 2  is alkyl or alkoxy, and 
     x is oxygen or sulfur and 
     n is 0, 1, 2 or 3. 
     The compounds have a strong herbicidal effect against various weeds together with a broad selectivity in regard to agricultural plants, particularly potatoes, cotton, peanuts, carrots and rice.

This is a continuation, of application Ser. No. 101,051, filed Dec. 6, 1979 which in turn is a continuation of Ser. No. 925 552, filed July 17, 1978.

BACKGROUND OF THE INVENTION

The invention relates to diurethanes, herbicidal compositions containing the same and a process for making same.

Diurethanes have already been used in the prior art for suppression of weeds such as for instance 3-methylcarbanilic acid-[3-(methoxycarbonylamino)-phenyl]-ester and the carbanilic acid-(3-(ethoxycarbonylamino)-phenyl)ester (West German Pat. No. 1,567,151).

These agents have a comparatively narrow spectrum of activity, though they have a superior selectivity when used in beta-beet cultures.

It is an object of the present invention to provide for an agent which has a broader spectrum of activity and is particularly selective towards potatoes, cotton, peanuts, carrots and rice.

SUMMARY OF THE INVENTION

This object is solved by a composition which contains at least one compound of the formula ##STR2## in which R is alkyl, alkenyl, alkinyl, halogenoalkyl or alkoxyalkyl,

R₁ is alkoxyalkyl or dialkoxyalkyl,

R₂ is alkyl or alkoxy,

X is oxygen or sulfur, and

n is 0, 1, 2 or 3.

The compounds are active against many undesirable plant families such as Digitalis, Valerianella, Trifolium, Portulaca, Papaver, Kochia, Solanum, Escholtzia, Euphorbia, Brassica, Datura, Ipomea, Setaria, Agrostis, Alopecurus, Bromus, Echinochloa, Digitaria.

The amounts used for the selective weed suppression are about 0.5 to 5 kg of active agent per 2.5 acres.

The diurethanes of the invention surprisingly and contrary to the prior art compounds of an analogous constitution can be used also in non-best cultures, for instance in cultures involving potatoes, cotton, peanuts, carrots, rice and others without causing any damage. This, of course, is of substantial economic importance.

Among the diurethanes of the invention those are superior in regard to herbicidal and selective activity in which in the above formula I, R is C₁ -C₄ -alkyl, C₂ -C₄ -alkenyl, C₃ -C₄ -alkinyl, halogen-C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl and R₁ is C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or di-C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, and R₂ is C₁ -C₃ -alkyl or C₁ -C₃ -alkoxy.

The diurethanes of the invention can either be used singly or intermixed with each other or in mixture with other active agents. Depending on the particular purpose there are for instance the following herbicidal agents which, if desired, can be added immediately prior to application of the compounds of the invention:

substituted anilines,

substituted aryloxycarbonylic acids and their salts, esters and amides,

substituted ethers,

substituted arsonic acids and their salts, esters and amides,

substituted benzimidazoles,

substituted benzisothiazoles,

substituted benzthiadiazinone dioxides,

substituted benzoxazines,

substituted benzoxazinones,

substituted benzthiazoles,

substituted benzthiadiazoles,

substituted biurets,

substituted quinolines,

substituted carbamates,

substituted aliphatic carboxylic acids and their salts, esters and amides,

substituted aromatic carboxylic acids and their salts, esters and amides,

substituted carbamoylalkyl-thio- or dithiophosphates,

substituted quinazolines,

substituted cycloalkylamidocarbonylthiol acids and their salts, esters and amides,

substituted cycloalkylcarboxylamido-thiazoles,

substituted dicarboxylic acids and their salts, esters and amides,

substituted dihydrobenzofuranylsulfonates,

substituted disulfides,

substituted dipyridylium salts,

substituted dithiocarbamates,

substituted dithiophosphoric acids and their salts, esters and amides,

substituted urea derivatives,

substituted hexahydro-1H-carbothioates,

substituted hydantoines,

substituted hydrazides,

substituted hydrazonium salts,

substituted isoxazolpyrimidones,

substituted imidazoles,

substituted isothiazolpyrimidones,

substituted ketones,

substituted naphthoquinones,

substituted aliphatic nitriles,

substituted aromatic nitriles,

substituted oxadiazoles,

substituted oxadiazinons,

substituted oxadiazolidinediones,

substituted oxadiazinediones,

substituted phenols and their salts and esters,

substituted phosphonic acids and their salts, esters and amides,

substituted phosphoniumchlorides,

substituted phosphonalkylglycines,

substituted phosphites,

substituted phosphoric acids and their salts, ester and amides,

substituted piperidines,

substituted pyrazoles,

substituted pyrazolalkylcarboxylic acids and their salts, esters, and amides,

substituted pyrazolium salts,

substituted pyrazoliumalkylsulfates,

substituted pyridazines,

substituted pyridazones,

substituted pyridine-carboxylic acids and their salts, esters and amides,

substituted pyridines,

substituted pyridinecarboxylates,

substituted pyridinones,

substituted pyrimidones,

substituted pyrrolidine-carboxylic acids and their salts, esters and amides,

substituted pyrrolidines,

substituted arylsulfonic acids and their salts, esters and amides,

substituted styrenes,

substituted tetrahydro-oxadiazindiones,

substituted tetrahydromethanoindenes,

substituted tetrahydro-diazol-thiones,

substituted tetrahydro-thiadiazine-thiones,

substituted tetrahydro-thiadiazolediones,

substituted thiadiazoles,

substituted aromatic thiocarboxylic acid amides,

substituted thiocarboxylic acids and their salts, esters and amides,

substituted thiolcarbamates,

substituted thiophosphoric acids and their salts, esters and amides,

substituted triazines,

substituted triazoles

substituted uracils, and

substituted urothidindiones.

In addition, other additives can also be used, for instance, non-phytotoxic additives which result in a synergistic increase of activity in herbicides, like wetting agents, emulsifiers, solvents and oily additives.

It is preferred to use the compounds of the inventions or mixtures thereof in the form of compositions such as powders, dusting agents, granulates, solutions, emulsions or suspensions. Liquid and/or solid carrier materials or diluents should be added and, if desired, wetting agents, adhesion promoting agents, emulsifiers, and/or dispersants can also be added.

Suitable liquid carrier materials are, for instance, water, aliphatic and aromatic hydrocarbons, such as, benzene, toluene, xylene, cyclohexanone, isophorone, dimethylsulfoxide, dimethylformamide, and furthermore, mineral oil fractions.

As solid carrier materials there are suitable mineral earths, for instance, tonsil, silicagel, talc, kaolin, attaclay, limestone, silicic acid, and plant products, such as for instance flours.

They may also be added surface active agents as for instance calciumlignosulfonate, polyoxyethylenealkyl-phenylether, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensation products, fatty alcohol sulfates, and substituted benzolsulfonic acids and their salts.

The amounts of the agent or agents of the invention and the different compositions can be varied within wide limits. The compositions may for instance contain about 10 to 80% by weight of active agents, about 90 to 20% by weight of liquid or solid carrier materials and up to 20 weight percent of surface active agents in which case a corresponding reduction of the carrier materials would take place.

The application of the compounds can be effected in conventional form, for instance with water as carrier materials in spray amounts of about 100 to 1000 liters per about 2.5 acres. The application of the compounds is possible by the so-called "low volume" and "ultra low volume" method and in the form of so-called microgranulates.

PROCESS OF MAKING THE COMPOUNDS

The diurethanes of above formula I can be made by different processes.

I. Compounds of the formula ##STR3## can be reacted with amines of the formula ##STR4## in the presence of an acid acceptor, for instance by adding an excess of the amine or an inorganic base, like sodium hydroxide, sodium carbonate, or potassium carbonate, or by adding a tertiary organic base such as triethylamine.

II. Compounds of the formula ##STR5## can also be reacted with carbamoylchlorides of the formula ##STR6## at temperature of 0° to 100° C. in the presence of a tertiary organic base such as triethylamine or pyridine or also as alkali salts, for instance, as sodium or potassium salts, and the compounds may be dissolved in a solvent such as methylisobutylketone or aceticethylester.

III. Compounds of the formula ##STR7## may also be hydrogenated in the presence of a catalyst, for instance nickel in a solvent like methanol to form the corresponding amine. The latter product is then reacted with compounds of the formula ##STR8## to form the desired products of the invention. This reaction is also carried out in the presence of an acid acceptor, for instance an inorganic base, like sodium hydroxide, sodium carbonate or potassium carbonate, or in the presence of a tertiary organic base, for instance triethylamine, and the reactants are dissolved in a solvent, for instance, acetic ethylester.

The products obtained in all cases are then isolated in conventional manner. In all of the processes just described R, R₁, R₂, X and n have the same meaning as in above formula I.

PREFERRED EMBODIMENTS OF THE INVENTION

The following examples will illustrate the making of the compounds of the invention.

EXAMPLE 1 N-(2,2-dimethoxyethyl)-3-methylcarbanilic acid-[3-(methoxycarbonylamino)-phenyl]-ester (Compound No. 1)

A solution of 26 g (0.1 mol) of chloroformic acid-3-methoxycarbonylamino-phenylester is added dropwise with a solution of 13.8 g of potassium carbonate in 50 ml water to a solution of 19.5 g (0.1 mol) of N-(2,2-dimethoxyethyl)-3-toluidene in 50 ml acetic ethylester while stirring and cooling the mixture to 10° to 15° C. The mass is then further subjected to stirring for another 30 minutes at 15° C. The organic phase is then separated, is diluted with 100 ml of acetic ester and is washed at 0° C. with a small amount of dilute sodium hydroxide, dilute hydrochloric acid and water.

After drying on magnesium sulfate the mass is concentrated in a partial vacuum. After adding isopropyl ether the reaction products are subjected to crystallization. The yield is 23.6 g=61% of the calculated value; m.p. 70° to 72° C.

In an analogous manner the following diurethanes were produced:

    ______________________________________                                         Com-                                                                           pound                          Physical                                        No.   Name of Compound         constants                                       ______________________________________                                         2.    N--(2-methoxyethyl)-carbanilic acid-                                                                    m.p.:                                                 (3-(methoxycarbonylamino)-phenyl-                                                                       116-118° C.                                    ester                                                                    3.    N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(methoxycarbonylamino)-                                                                         115-117° C.                                    phenyl)-ester                                                            4.    N--(2-methoxyethyl)-3-methylcarbanilic                                                                  m.p.:                                                 acid-(3-(methoxycarbonylamino)-phenyl)-                                                                 86-89° C.                                      ester                                                                    5.    N--(2-methoxyethyl)-carbanilic acid-                                                                    m.p.:                                                 (3-(ethoxycarbonylamino)-phenyl)-                                                                       70-71° C.                                      ester                                                                    6.    N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-isopropoxycarbonylamino)-                                                                       85-87° C.                                      phenyl)-ester                                                            7.    N--(2-methoxyethyl)-carbanilic acid-                                                                    m.p.:                                                 (3-(isopropoxycarbonylamino)-                                                                           65-67° C.                                      phenyl)-ester                                                            8.    N--(2-methoxyethyl)-carbanilic                                                                          n.sub.D.sup.20 : 1.5131                               acid-(3-(sec.-butoxycarbonyl-                                                  amino)-phenyl)-ester                                                     9.    N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(isobutylcarbonylamino)-                                                                        94-95° C.                                      phenyl)-ester                                                            10.   N--(2-methoxyethyl)-carbanilic                                                                          m.p.:                                                 acid-(3-(2-methylpropoxycarbonyl-                                                                       72-74° C.                                      amino)-phenyl)-ester                                                     11.   N--(2-methoxyethyl)-carbanilic acid-                                                                    n.sub.D.sup.20 : 1.5398                               (3-(allyloxycarbonylamino)-phenyl)-                                            ester                                                                    12.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(allyloxycarbonylamino)-                                                                        76-78° C.                                      phenyl)-ester                                                            13.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(2-propinyloxycarbonyl-                                                                         122° C.                                        amino)-phenyl)-ester                                                     14.   N--(2-methoxyethyl)-carbanilic                                                                          n.sub.D.sup.20 : 1.5448                               acid-(3-(2-propinyloxycarbonyl-                                                amino)-phenyl)-ester                                                     15.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(methylthiocarbonylamino)-                                                                      100-102° C.                                    phenyl)-ester                                                            16.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(ethylthiocarbonylamino)-                                                                       85-87° C.                                      phenyl)-ester                                                            17.   N--(2-methoxyethyl)-carbanilic                                                                          m.p.:                                                 acid-(3-ethylthiocarbonylamino)-                                                                        88-89° C.                                      phenyl)-ester                                                            18.   N--(2-ethoxyethyl)-carbanilic acid-                                                                     m.p.:                                                 (3-methoxycarbonylamino)-phenyl)-                                                                       116-117° C.                                    ester                                                                    19.   N--(2-ethoxyethyl)-3-methylcarbanilic                                                                   m.p.:                                                 acid-(3-(methoxycarbonylamino)-phenyl)-                                                                 78-79° C.                                      ester                                                                    20.   N--(2,2-dimethoxyethyl)-3-methyl-                                                                       m.p.:                                                 carbanilic acid-(3-(methoxycarbonyl-                                                                    70-72° C.                                      amino)-phenyl)-ester                                                     21.   N--(2,2-dimethoxyethyl)-4-methyl-                                                                       n.sub.D.sup.20 : 1.7071                               carbanilic acid-(3-(methoxycarbonyl-                                           amino)-phenyl)-ester                                                     22.   N--(2-methoxyethyl)-3-methyl-                                                                           n.sub.D.sup.20 : 1.5559                               carbanilic acid-(3-(ethoxycarbonyl-                                            amino)-phenyl)-ester                                                     23.   N--(2-ethoxyethyl)-carbanilic acid-                                                                     m.p.:                                                 (3-(ethoxycarbonylamino)-phenyl)-                                                                       48-50° C.                                      ester                                                                    24.   N--(2,2-dimethoxyethyl)-3-methyl-                                                                       m.p.:                                                 carbanilic acid-(3-(ethoxycarbonyl-                                                                     75-78° C.                                      amino)-phenyl)-ester                                                     25.   N--(2-ethoxyethyl)-3-methylcarbanilic                                                                   m.p.:                                                 acid-(3-ethoxycarbonylamino)-phenyl)-                                                                   83-84° C.                                      ester                                                                    26.   N--(2,2-dimethoxyethyl)-4-methyl-                                                                       m.p.:                                                 carbanilic acid-(3-ethoxycarbonyl-                                                                      88-89° C.                                      amino)-phenyl)-ester                                                     27.   N-(2,2-dimethoxyethyl)-4-methyl-                                                                        m.p.:                                                 carbanilic acid-(3-isopropoxycarbonyl-                                                                  87-88° C.                                      amino)-phenyl)-ester                                                     28.   N--(2,2-dimethoxyethyl)-3-methyl-                                                                       m.p.: 96° C.                                   carbanilic acid-(3-(1-methylethoxy-                                            carbonylamino)-phenyl)-ester                                             29.   N--(2,2-dimethoxyethyl)-4-methylcar-                                                                    m.p.: 68° C.                                   banilic acid-(3-butoxycarbonylamino)-                                          phenyl)-ester                                                            30.   N--(2,2-dimethoxyethyl)-3-methylcar-                                                                    m.p.:                                                 banilic acid-(3-(2-methylpropoxy-                                                                       112-113° C.                                    carbonylamino)-phenyl)-ester                                             31.   N--(2,2-dimethoxyethyl)-3-methyl-                                                                       m.p.:                                                 carbanilic acid-(3-(1-methylpropoxy-                                                                    94-95° C.                                      carbonylamino)-phenyl)-ester                                             32.   N--(2,2-dimethoxyethyl)-4-methylcarba-                                                                  m.p.:                                                 nilic acid-(3-(2-methylpropoxycarbonyl-                                                                 103° C.                                        amino)-phenyl)-ester                                                     33.   N--(2,2-dimethoxyethyl)-3-methylcar-                                                                    m.p.:                                                 banilic acid-(3-(2-methoxyethoxycar-                                                                    78-80° C.                                      bonylamino)-phenyl)-ester                                                34.   N--(2,2-dimethoxyethyl)-3-methylcar-                                                                    m.p.:                                                 banilic acid-(3-allyloxycarbonylamino)-                                                                 78-80° C.                                      phenyl)-ester                                                            35.   N--(2,2-dimethoxyethyl)-3-methylcar-                                                                    m.p.:                                                 banilic acid-(3-(2-propinyloxycarbonyl-                                                                 103-106° C.                                    amino)-phenyl)-ester                                                     36.   N--(2,2-dimethoxyethyl)-4-methylcar-                                                                    m.p.:                                                 banilic acid-(3-(2-propinyloxycarbonyl-                                                                 89-90° C.                                      amino)-phenyl)-ester                                                     37.   N--(2-methoxyethyl)-carbanilic acid-                                                                    m.p.:                                                 (3-methylthiocarbonylamino)-phenyl)-                                                                    98-100° C.                                     ester                                                                    38.   N--(2,2-dimethoxyethyl)-4-methylcar-                                                                    m.p.:                                                 banilic acid-(3-(methylthio-carbonyl-                                                                   79-80° C.                                      amino)-phenyl)-ester                                                     39.   N--(2,2-dimethoxyethyl)-3-methylcar-                                                                    m.p.:                                                 banilic acid-(3-methylthiocarbonyl-                                                                     107° C.                                        amino)-phenyl)-ester                                                     40.   N--(2,2-dimethoxyethyl)-3-methylcar-                                                                    m.p.:                                                 banilic acid-(3-(ethylthiocarbonyl-                                                                     79-82° C.                                      amino)-phenyl)-ester                                                     41.   N--(2,2-dimethoxyethyl)-4-methylcar-                                                                    m.p.: 81° C.                                   banilic acid-(3-(ethylthiocarbonyl-                                            amino)-phenyl)-ester                                                     42.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(ethoxycarbonylamino)-phenyl-                                                                   70-73° C.                                      ester                                                                    43.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(sec.-butoxycarbonylamino)-                                                                     80-82° C.                                      phenyl)-ester                                                            44.   N--(2-methoxyethyl)-4-methylcarbani-                                                                    m.p.: 78° C.                                   lic acid-(3-(ethoxycarbonylamino)-                                             phenyl)-ester                                                            45.   N--(2-ethoxyethyl)-2-methylcarbanilic                                                                   m.p.:                                                 acid-(3-ethoxycarbonylamino)-phenyl-                                                                    65-68° C.                                      ester                                                                    46.   N--(2-methoxyethyl)-4-methylcarbanilic                                                                  m.p.:                                                 acid-(3-(methoxycarbonylamino)-phenyl)-                                                                 89-90° C.                                      ester                                                                    47.   N--(2-ethoxyethyl)-2-methylcarbanilic                                                                   m.p.:                                                 acid-(3-(methoxycarbonylamino)-                                                                         118-120° C.                                    phenyl)-ester                                                            48.   3-methyl-N--(2-propoxyethyl)-car-                                                                       m.p.:                                                 banilic acid-(3-(ethoxycarbonyl-                                                                        67-69° C.                                      amino)-phenyl)-ester                                                     49.   2-methyl-N--(2-propoxyethyl)-carbanil-                                                                  m.p.:                                                 ic acid-(3-(methoxycarbonylamino)-                                                                      76-78° C.                                      phenyl)-ester                                                            50.   N--(2,2-dimethoxyethyl)-2-methyl-                                                                       m.p.:                                                 carbanilic acid-(3-(2-propinyloxycar-                                                                   105-107° C.                                    bonylamino)-phenyl)-ester                                                51.   N--(2,2-dimethoxyethyl)-4-methyl-                                                                       n.sub.D.sup.20 : 1.7679                               carbanilic acid-(3-(1-methylpropoxy-                                           carbonylamino)-phenyl)-ester                                             52.   N--(2-methoxyethyl)-4-methoxycar-                                                                       m.p.:                                                 banilic acid-(3-methoxycarbonylamino)-                                                                  93-94° C.                                      phenyl)-ester                                                            53.   N--(2-ethoxyethyl)-4-methylcarbanilic                                                                   m.p.:                                                 acid-(3-(methoxycarbonylamino)-phenyl)-                                                                 102-103° C.                                    ester                                                                    54.   N--(2-ethoxyethyl)-4-methylcarbanilic                                                                   m.p.:                                                 acid-(3-(ethoxycarbonylamino)-phenyl)-                                                                  68-70° C.                                      ester                                                                    55.   N--(2,2-dimethoxyethyl)-4-methylcar-                                                                    n.sub.D.sup.20 : 1.5145                               banilic acid-(3-(allyloxycarbonyl-                                             amino)-phenyl)-ester                                                     56.   N--(2-butoxyethyl)-4-methylcarban-                                                                      n.sub.D.sup.20 : 1.5391                               ilic acid-(3-(ethoxycarbonylamino)-                                            phenyl)-ester                                                            57.   4-methoxy-N--(2-methoxyethyl)-                                                                          n.sub.D.sup.20 : 1.5520                               carbanilic acid-(3-(ethoxycarbonyl-                                            amino)-phenyl)-ester                                                     58.   N--(2-propoxyethyl)-carbanilic                                                                          n.sub.D.sup.20 : 1.5441                               acid-(3-(methoxycarbonylamino)-                                                phenyl)-ester                                                            59.   2-methyl-N--(2-methoxyethyl)-carban-                                                                    m.p.:                                                 ilic acid-(3-(methoxycarbonylamino)-                                                                    110-111° C.                                    phenyl)-ester                                                            60.   3-methyl-N--(2-propoxyethyl)-car-                                                                       n.sub.D.sup.20 : 1.5490                               banilic acid-(3-(methoxycarbonyl-                                              amino)-phenyl)-ester                                                     61.   N--(2-butoxyethyl)-4-methylcarbani-                                                                     n.sub.D.sup.20 : 1.5427                               lic acid-(3-(methoxycarbonylamino)-                                            phenyl)-ester                                                            62.   3-methoxy-N--(2-methoxyethyl)-car-                                                                      n.sub.D.sup.20 : 1.5566                               banilic acid-(3-methoxycarbonyl-                                               amino)-phenyl)-ester                                                     63.   N--(2-butoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5390                               (3-(methoxycarbonylamino)-phenyl)-                                             ester                                                                    64.   4-methyl-N--(2-propoxyethyl)-car-                                                                       m.p.:                                                 banilic acid-(3-(methoxycarbonyl-                                                                       62-63° C.                                      amino)-phenyl)-ester                                                     65.   N--(2-methoxyethyl)-2-methylcar-                                                                        m.p.:                                                 banilic acid-(3-(ethoxycarbonyl-                                                                        98-100° C.                                     amino)-phenyl)-ester                                                     66.   N--(2-methoxyethyl)-2-methylcarbani-                                                                    m.p.:                                                 lic acid-(3-(ethylthiocarbonylamino)-                                                                   115-117° C.                                    phenyl)-ester                                                            67.   N--(2-methoxyethyl)-3-methylcarbani-                                                                    m.p.:                                                 lic acid-(3-(1-methylethoxycarbonyl-                                                                    93-94° C.                                      amino)-phenyl)-ester                                                     68.   N--(2-methoxyethyl)-3-methylcarbani-                                                                    m.p.:                                                 lic acid-(3-(2-propinyloxycarbonyl-                                                                     90-92° C.                                      amino)-phenyl)-ester                                                     69.   N--(2-butoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5340                               (3-(ethoxycarbonylamino)-phenyl)-                                              ester                                                                    70.   3-methoxy-N--(2-methoxyethyl)-carbani-                                                                  n.sub.D.sup.20 : 1.5552                               lic acid-(3-(ethoxycarbonylamino)-                                             phenyl)-ester                                                            71.   N--(2-methoxyethyl)-3-methylcarbani-                                                                    n.sub.D.sup.20 : 1.5716                               lic acid-(3-(ethylthio-carbonylamino)-                                         phenyl)-ester                                                            72.   N--(2-methoxyethyl)-3-methylcarbanilic                                                                  n.sub.D.sup.20 : 1.5439                               acid-(3-(2-methylpropoxycarbonyl-                                              amino)-phenyl)-ester                                                     73.   N--(2-ethoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5354                               (3-(2-methylpropoxycarbonylamino)-                                             phenyl)-ester                                                            74.   N--(2-ethoxyethyl)-3-methylcarbani-                                                                     n.sub.D.sup.20 : 1.5383                               lic acid-(3-(2-methylpropoxycar-                                               bonylamino)-phenyl)-ester                                                75.   N--(2-ethoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5419                               (3-(1-methylpropoxycarbonylamino)-                                             phenyl)-ester                                                            76.   N--(2-methoxyethyl)-carbanilic acid-                                                                    m.p.:                                                 (3-(1-methyl-2-chloroethoxycarbonyl-                                                                    109° C.                                        amino)-phenyl)-ester                                                     77.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      m.p.:                                                 acid-(3-(1-methyl-2-chloroethoxy-                                                                       88-89° C.                                      carbonylamino)-phenyl)-ester                                             78.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      n.sub.D.sup.20 : 1.5528                               acid-(3-(2-bromoethoxycarbonyl-                                                amino)-phenyl)-ester                                                     79.   N--(2,2-dimethoxyethyl)-carbanilic                                                                      n.sub.D.sup.20 : 1.5379                               acid-(3-(2-methoxyethoxycarbonyl-                                              amino)-phenyl)-ester                                                     80.   N--(2-methoxyethyl)-2-methylcarbani-                                                                    m.p.:                                                 lic acid-(3-(methylthio-carbonyl-                                                                       110-112° C.                                    amino)-phenyl)-ester                                                     81.   3-methyl-N--(2-propoxyethyl)-car-                                                                       n.sub.D.sup.20 : 1.5374                               banilic acid-(3-(2-methylpropoxy-                                              carbonylamino)-phenyl)-ester                                             82.   N--(2-methoxyethyl)-4-methylcarbanilic-                                                                 n.sub.D.sup.20 : 1.5456                               acid-(3-(2-methylpropoxycarbonylamino)-                                        phenyl)-ester                                                            83.   N--(2-methoxyethyl)-3-methylcar-                                                                        m.p.:                                                 banilic acid-(3-(2-methylpropoxy-                                                                       74-75° C.                                      carbonylamino)-phenyl)-ester                                             84.   N--(2-methoxyethyl)-4-methylcarbani-                                                                    m.p.:                                                 lic acid-(3-(methylthio-carbonylamino)-                                                                 107-109° C.                                    phenyl)-ester                                                            85.   N--(2-ethoxyethyl)-3-methylcarbanilic                                                                   m.p.:                                                 acid-(3-(methylthio-carbonylamino)-                                                                     93-95° C.                                      phenyl)-ester                                                            86.   N--(2-butoxyethyl)-4-methylcarbanilic                                                                   n.sub.D.sup.20 : 1.5593                               acid-(3-(methylthio-carbonylamino)-                                            phenyl)-ester                                                            87.   N--(2-ethoxyethyl)-2-methylcarbani-                                                                     n.sub.D.sup.20 : 1.5786                               lic acid-(3-(methylthio-carbonyl-                                              amino)-phenyl)-ester                                                     88.   N--(2-ethoxyethyl)-carbanilic acid-                                                                     m.p.:                                                 (3-(methylthio-carbonylamino)-phenyl)-                                                                  82-84° C.                                      ester                                                                    89.   N--(2-methoxyethyl)-3-methoxycarbani-                                                                   n.sub.D.sup.20 : 1.5868                               lic acid-(3-(methylthio-carbonyl-                                              amino)-phenyl)-ester                                                     90.   N--(2-butoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5550                               (3-(methylthio-carbonylamino)-phenyl)-                                         ester                                                                    91.   N--(2-methoxyethyl)-4-methoxycar-                                                                       n.sub.D.sup.20 : 1.5727                               banilic acid-(3-(ethylthio-carbonyl-                                           amino)-phenyl)-ester                                                     92.   N--(2-methoxyethyl)-4-methoxycarbani-                                                                   n.sub.D.sup.20 : 1.5482                               lic acid-(3-(1-methylethoxycarbonyl-                                           amino)-phenyl)-ester                                                     93.   N-- (2-methoxyethyl)-4-methoxycarbani-                                                                  n.sub.D.sup.20 : 1.5597                               lic acid-(3-(2-propinyloxycarbonyl-                                            amino)-phenyl)-ester                                                     94.   N--(2-methoxyethyl)-4-methoxycarbani-                                                                   n.sub.D.sup.20 : 1.5420                               lic acid-(3-(1-methylpropoxycarbonyl-                                          amino)-phenyl)-ester                                                     95.   N--(2-methoxyethyl)-4-methoxycarbani-                                                                   n.sub.D.sup.20 : 1.5483                               lic acid-(3-(2-methylpropoxycarbonyl-                                          amino)-phenyl)-ester                                                     96.   3-methyl-N--(2-propoxyethyl)-carbani-                                                                   m.p.:                                                 lic acid-(3-(methylthio-carbonylamino)-                                                                 74-75° C.                                      phenyl)-ester                                                            97.   4-methoxy-N--(2-methoxyethyl)-car-                                                                      m.p.:                                                 banilic acid-(3-(methylthiocarbonyl-                                                                    98-100° C.                                     amino)-phenyl)-ester                                                     98.   N--(2,2-diethoxyethyl)-carbanilic                                                                       m.p.:                                                 acid-[3-(methoxycarbonylamino)-                                                                         82-83° C.                                      phenyl]-ester                                                            99.   N--(2,2-diethoxyethyl)-carbanilic                                                                       m.p.: 84° C.                                   acid-[3-(ethylthio-carbonylamino)-                                             phenyl]-ester                                                            100.  N--(2-ethoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5538                               [3-(allyloxycarbonylamino)-phenyl]-                                            ester                                                                    101.  N--(2-ethoxyethyl)-3-methylcarbani-                                                                     n.sub.D.sup.20 : 1.5533                               lic acid-[3-(allyloxycarbonyl-                                                 amino)-phenyl]-ester                                                     102.  N--(2-propoxyethyl)-carbanilic acid-                                                                    n.sub.D.sup.20 : 1.5458                               [3-(allyloxycarbonylamino)-phenyl]-                                            ester                                                                    103.  N--(methoxyethyl)-carbanilic acid-                                                                      n.sub.D.sup.20 : 1.5574                               [3-(2-bromoethoxycarbonylamino)-                                               phenyl]-ester                                                            104.  N--(2-butoxyethyl)-3-methylcarbani-                                                                     n.sub.D.sup.20 : 1.5429                               lic acid-[3-(methoxycarbonylamino)-                                            phenyl]-ester                                                            105.  N--(2-butoxyethyl)-3-methylcarbanil-                                                                    n.sub.D.sup.20 : 1.5394                               ic acid-[3-(ethoxycarbonylamino)-                                              phenyl]-ester                                                            106.  N--(2,2-diethoxyethyl)-carbanilic                                                                       n.sub.D.sup.20 : 1.7010                               acid-[3-(ethoxycarbonylamino)-                                                 phenyl]-ester                                                            107.  N--(2-propoxyethyl)-carbanilic                                                                          n.sub.D.sup.20 : 1.5355                               acid-[3-(1-methylethoxycarbonyl-                                               amino)-phenyl]-ester                                                     108.  N--(2-butoxyethyl)-3-methylcarbani-                                                                     n.sub.D.sup.20 : 1.5345                               lic acid-[3-(1-methylethoxycarbonyl-                                           amino)-phenyl]-ester                                                     109.  3-methyl-N--(2-propoxyethyl)-carbani-                                                                   m.p.:                                                 lic acid-[3-(1-methylethoxycarbonyl-                                                                    83-85° C.                                      amino)-phenyl]-ester                                                     110.  N--(2-butoxyethyl)-4-methylcarbanil-                                                                    n.sub.D.sup.20 : 1.5241                               ic acid-[3-(1-methylethoxycarbonyl-                                            amino)-phenyl]-ester                                                     111.  N--(2-butoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5289                               [3-(1-methylethoxycarbonylamino)-                                              phenyl]-ester                                                            112.  N--(2,2-diethoxyethyl)-carbanilic                                                                       n.sub.D.sup.20 : 1.6388                               acid-[3-(allyloxycarbonylamino)-                                               phenyl]-ester                                                            113.  N--(2-methoxyethyl)-2-methylcarbanil-                                                                   m.p.:                                                 ic acid-[3-(2-propenyloxycarbonyl-                                                                      88-90° C.                                      amino)-phenyl]-ester                                                     114.  N--(2,2-diethoxyethyl)-carbanilic                                                                       n.sub.D.sup.20 : 1.6900                               acid-[3-(2-methylpropoxycarbonyl-                                              amino)-phenyl]-ester                                                     115.  N--(2,2-diethoxyethyl)-carbanilic                                                                       n.sub.D.sup.20 : 1.6873                               acid-[3-(2-propinyloxycarbonyl-                                                amino)-phenyl]-ester                                                     116.  N--(2-ethoxyethyl)-4-methylcarbanil-                                                                    m.p.:                                                 ic acid-[3-(methylthiocarbonylamino)-                                                                   104-105° C.                                    phenyl]-ester                                                            117.  N--(2,2-diethoxyethyl)-carbanilic                                                                       m.p.: 83° C.                                   acid-[3-(methylthio-carbonylamino)-                                            phenyl]-ester                                                            118.  4-methyl-N--(2-propoxyethyl)-carbanili-                                                                 m.p.:                                                 ic acid-[3-(methylthio-carbonylamino)-                                                                  103-104° C.                                    phenyl]-ester                                                            119.  2-methyl-N--(2-propoxyethyl)-carbanil-                                                                  n.sub.D.sup.20 : 1.5681                               ic acid-[3-(methylthio-carbonylamino)-                                         phenyl]-ester                                                            120.  N--(2-butoxyethyl)-3-methylcarbanil-                                                                    n.sub.D.sup.20 : 1.5648                               ic acid-[3-(methylthio-carbonylamino)-                                         phenyl]-ester                                                            121.  N--(2-propoxyethyl)-carbanilic acid-                                                                    n.sub.D.sup.20 : 1.5694                               [3-(ethylthio-carbonylamino)-phenyl]-                                          ester                                                                    122.  3-methyl-N--(2-propoxyethyl)-carbanil-                                                                  n.sub.D.sup.20 : 1.5683                               ic acid-[3-(ethylthio-carbonylamino)-                                          phenyl]-ester                                                            123.  N--(2-butoxyethyl)-3-methylcarbanilic                                                                   n.sub.D.sup.20 : 1.5588                               acid-[3-(ethylthio-carbonylamino)-                                             phenyl]-ester                                                            124.  N--(2-butoxyethyl)-4-methylcarbanil-                                                                    m.p.:                                                 ic acid-[3-ethylthio-carbonylamino)-                                                                    62-64° C.                                      phenyl]-ester                                                            125.  N--(2-cyanoethyl)-3-chlorocarbanilic                                                                    n.sub.D.sup.20 : 1.5605                               acid-(3-(allyloxycarbonylamino)-                                               phenyl)-ester                                                            126.  3-methyl-N--(2-propoxyethyl)-carbanil-                                                                  m.p.:                                                 ic acid-(3-(2-propinyloxycarbonyl-                                                                      84-86° C.                                      amino)-phenyl)-ester                                                     127.  N--(2-propoxyethyl)-carbanilic acid-                                                                    n.sub.D.sup.20 : 1.5477                               (3-(2-propinyloxycarbonylamino)-                                               phenyl)-ester                                                            128.  N--(2-butoxyethyl)-4-methylcarbanil-                                                                    n.sub.D.sup.20 : 1.5472                               ic acid-(3-(2-propinyloxycarbonyl-                                             amino)-phenyl)-ester                                                     129.  N--(2-butoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5418                               (3-(2-propinyloxycarbonylamino)-                                               phenyl)-ester                                                            130.  2-methyl-N--(2-propoxyethyl)-carbanil-                                                                  n.sub.D.sup.20 : 1.5472                               ic acid-(3-(2-propinyloxycarbonylamino)-                                       phenyl)-ester                                                            131.  N--(2-butoxyethyl)-3-methylcarbanil-                                                                    n.sub.D.sup.20 : 1.5451                               ic acid-(3-(2-propinyloxycarbonyl-                                             amino)-phenyl)-ester                                                     132.  4-methyl-N--(2-propoxyethyl)-carbanil-                                                                  m.p.:                                                 ic acid-(3-(2-propinyloxycarbonyl-                                                                      73-75° C.                                      amino)-phenyl)-ester                                                     133.  N--(2-ethoxyethyl)-carbanilic acid-                                                                     m.p.:                                                 (3-(ethylthiocarbonylamino)-phenyl-                                                                     92-93° C.                                      ester                                                                    134.  N--(2-ethoxyethyl)-3-methylcarbanil-                                                                    n.sub.D.sup.20 : 1.5675                               ic acid-(3-ethylthiocarbonylamino)-                                            phenyl)-ester                                                            135.  2-methyl-N--(2-propoxyethyl)-carbanil-                                                                  n.sub.D.sup.20 : 1.5578                               ic acid-(3-ethylthiocarbonylamino)-                                            phenyl)-ester                                                            136.  N--(2-ethoxyethyl)-4-methylcarbanil-                                                                    n.sub.D.sup.20 : 1.5643                               ic acid-(3-(ethylthiocarbonylamino)-                                           phenyl)-ester                                                            137.  4-methyl-N--(2-propoxyethyl)-carbanil-                                                                  m.p.:                                                 ic acid-(3-(ethylthiocarbonylamino)-                                                                    72-74° C.                                      phenyl)-ester                                                            138.  N--(2-methoxyethyl)-4-methylcarbanil-                                                                   m.p.:                                                 ic acid-(3-(ethylthiocarbonylamino)-                                                                    76-77° C.                                      phenyl)-ester                                                            139.  N--(2-ethoxyethyl)-2-methylcarbanil-                                                                    m.p.:                                                 ic acid-(3-(ethylthiocarbonylamino)-                                                                    88-90° C.                                      phenyl)-ester                                                            140.  N--(2-methoxyethyl)-3-methoxycarbanil-                                                                  m.p.:                                                 ic acid-(3-(ethylthio-carbonylamino)-                                                                   88-89° C.                                      phenyl)-ester                                                            141.  N--(2-methoxyethyl)-3-methylcarbanil-                                                                   n.sub.D.sup.20 : 1.5926                               ic acid-(3-(methylthio-carbonylamino)-                                         phenyl)-ester                                                            142.  2-methyl-N--(2-propoxyethyl)-carbanil-                                                                  n.sub.D.sup.20 : 1.5286                               ic acid-(3-(ethoxycarbonylamino)-                                              phenyl)-ester                                                            143.  N--(2-ethoxyethyl)-carbanilic acid-                                                                     n.sub.D.sup.20 : 1.5400                               (3-(1-methylethoxycarbonylamino)-                                              phenyl)-ester                                                            144.  N--(2-methoxyethyl)-4-methylcarbanil-                                                                   n.sub.D.sup.20 : 1.5357                               ic-(3-(1-methylethoxycarbonylamino)-                                           phenyl)-ester                                                            145.  N--(2-ethoxyethyl)-4-methylcarbanil-                                                                    n.sub.D.sup.20 : 1.5361                               ic acid-(3-(1-methylethoxycarbonyl-                                            amino)-phenyl)-ester                                                     146.  1-methyl-N--(2-propoxyethyl)-carbanil-                                                                  n.sub.D.sup.20 : 1.5328                               ic acid-(3-(1-methylethoxycarbonyl-                                            amino)-phenyl)-ester                                                     147.  4-methyl-N--(2-propoxyethyl)-carban-                                                                    n.sub.D.sup.20 : 1.5354                               ilic acid-(3-(1-methylethoxycarbonyl-                                          amino)-phenyl)-ester                                                     148.  4-methyl-N--(2-propoxyethyl)-carbanil-                                                                  m.p.:                                                 ic acid-(3-(ethoxycarbonylamino)-                                                                       78-80° C.                                      phenyl)-ester                                                            149.  N--(2-ethoxyethyl)-3-methylcarbanil-                                                                    m.p.:                                                 ic acid-(3-(1-methylethoxycarbonyl-                                                                     78-80° C.                                      amino)-phenyl)-ester                                                     150.  N--(2-ethoxyethyl)-2-methylcarbanilic                                                                   m.p.:                                                 acid-(3-(1-methylethoxycarbonyl-                                                                        79-81° C.                                      amino)-phenyl)-ester                                                     ______________________________________                                    

These compounds are soluble for instance in acetone, cyclohexanone, acetic acid ethylester, isophorone, tetrahydrofuran, dioxane, dimethylformamide and hexamethylphosphoric acid triamide. They are virtually insoluble in water and light gasoline.

The starting products for making the compounds of the invention according to the above processes are known or conventional.

The following examples will further illustrate the application and use of the compounds of the invention.

APPLICATION AND USES EXAMPLE 2

The compounds of the invention listed in the following Table I were applied in a hothouse in amounts of 5 kg of active agent per about 2.5 acres and dissolved in 600 liters of water per about 2.5 acres to Sinapis and Solanum as test plants. The application was effected by spraying the plants. The results were evaluated three weeks after treatment on a scale from 0=no effect to 4=total destruction of the plants.

As appears from Table I normally a destruction of the test plants was accomplished.

                  TABLE I                                                          ______________________________________                                         Compound of the Invention                                                                              Sinapis Solanum                                        ______________________________________                                         N--(2-methoxyethyl)-carbanilic acid-(3-                                                                4       4                                              (methoxycarbonylamino)-phenyl)-ester                                           N--(2,2-dimethoxyethyl)-carbanilic                                                                     4       4                                              acid-(3-(methoxycarbonylamino)-phenyl)-                                        ester                                                                          N--(2-methoxyethyl)-3-methylcarbanilic                                                                 4       4                                              acid-(3-(methoxycarbonylamino)-phenyl)-                                        ester                                                                          N--(2-methoxyethyl)-carbanilic acid-(3-                                                                4       4                                              (ethoxycarbonylamino)-phenyl)-ester                                            N--(2,2-dimethoxyethyl)-carbanilic acid-                                                               4       4                                              (3-isopropoxycarbonylamino)-phenyl)-                                           ester                                                                          N--(2-methoxyethyl)-carbanilic acid-                                                                   4       4                                              (3-(isopropoxycarbonylamino)-phenyl)-                                          ester                                                                          N--(2-methoxyethyl)-carbanilic acid-(3-                                                                4       4                                              (sec.-butoxycarbonylamino)-phenyl)-                                            ester                                                                          N--(2,2-dimethoxyethyl)-carbanilic acid-                                                               4       4                                              (3-(isobutylcarbonylamino)-phenyl)-ester                                       N--(2-methoxyethyl)-carbanilic acid-(3-                                                                4       4                                              (2-methylpropoxycarbonylamino)-phenyl)-                                        ester                                                                          N--(2-methoxyethyl)-carbanilic acid-(3-                                                                4       4                                              (allyloxycarbonylamino)-phenyl)-ester                                          N--(2,2-dimethoxyethyl)-carbanilic                                                                     4       4                                              acid-(3-(allyloxycarbonylamino)-phenyl)-                                       ester                                                                          N--(2,2-dimethoxyethyl)-carbanilic acid-                                                               4       4                                              (3-(2-propinyloxycarbonylamino)-phenyl)-                                       ester                                                                          N--(2-methoxyethyl)-carbanilic acid-                                                                   4       4                                              (3-(2-propinyloxycarbonylamino)-phenyl)-                                       ester                                                                          N--(2,2-dimethoxyethyl)-carbanilic acid-                                                               4       4                                              (3-(methylthiocarbonylamino)-phenyl)-                                          ester                                                                          N--(2,2-dimethoxyethyl)-carbanilic acid-                                                               4       4                                              (3-(ethylthiocarbonylamino)-phenyl)-ester                                      N--(2-methoxyethyl)-carbanilic acid-(3-                                                                4       4                                              ethylthiocarbonylamino)-phenyl)-ester                                          N--(2-ethoxyethyl)-carbanilic acid-(3-                                                                 4       4                                              methoxycarbonylamino)-phenyl)-ester                                            N--(2-ethoxyethyl)-3-methylcarbanilic                                                                  4       4                                              acid-(3-(methoxycarbonylamino)-phenyl)-                                        ester                                                                          N--(2,2-dimethoxyethyl)-3-methylcarbanilic                                                             4       4                                              acid-(3-(methoxycarbonylamino)-phenyl)-                                        ester                                                                          N--(2,2-dimethoxyethyl)-4-methylcarbanilic                                                             4       4                                              acid-(3-(methoxycarbonylamino)-phenyl)-                                        ester                                                                          N--(2-methoxyethyl)-3-methylcarbanilic-                                                                4       4                                              (3-(ethoxycarbonylamino)-phenyl)-ester                                         N--(2-ethoxyethyl)-carbanilic acid-(3-                                                                 4       4                                              (ethoxycarbonylamino)-phenyl)-ester                                            N--(2,2-dimethoxyethyl)-3-methylcarbanilic                                                             4       4                                              acid-(3-(ethoxycarbonylamino)-phenyl)-ester                                    N--(2-ethoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-ethoxycarbonylamino)-phenyl)-ester                                          N--(2,2-dimethoxyethyl)-4-methylcarbanilic                                                             4       4                                              acid-(3-ethoxycarbonylamino)-phenyl)-ester                                     N--(2,2-dimethoxyethyl)-4-methylcarbanilic                                                             4       4                                              acid-(3-(isopropoxycarbonylamino)-phenyl)-                                     ester                                                                          N--(2,2-dimethoxyethyl)-3-methylcarbanilic                                                             4       4                                              acid-(3-(1-methylethoxycarbonylamino)-                                         phenyl)-ester                                                                  N--(2,2-dimethoxyethyl)-4-methylcarbanilic                                                             4       4                                              acid-(3-butoxycarbonylamino)-phenyl)-ester                                     N--(2,2-dimethoxyethyl)-3-methcarbanilic                                                               4       4                                              acid-(3-(2-methylpropoxycarbonylamino)-                                        phenyl)-ester                                                                  N--(2,2-dimethoxyethyl)-3-methylcarbanilic                                                             4       4                                              acid-(3-(1-methylpropoxycarbonylamino)-                                        phenyl)-ester                                                                  N--(2,2-dimethoxyethyl)-4-methylcarbanilic                                                             4       4                                              acid-(3-(2-methylpropoxycarbonylamino)-                                        phenyl)-ester                                                                  N--(2,2-dimethoxyethyl)-3-methylcarbanilic                                                             4       4                                              acid-(3-(2-methoxyethoxycarbonylamino)-                                        phenyl)-ester                                                                  N--(2,2-dimethoxyethyl)-3-methylcarbanilic                                                             4       4                                              acid-(3-(allyloxycarbonylamino)-phenyl)-                                       ester                                                                          N--(2,2-dimethoxyethyl)-3-methylcarbanilic                                                             4       4                                              acid-(3-(2-propinyloxycarbonylamino)-phenyl)-                                  ester                                                                          N--(2,2-dimethoxyethyl)-4-methylcarbanilic                                                             4       4                                              acid-(3-(2-propinyloxycarbonylamino)-phenyl)-                                  ester                                                                          N--(2-methoxyethyl)-carbanilic acid-(3-                                                                4       4                                              methylthiocarbonylamino)-phenyl)-ester                                         N--(2,2-dimethoxyethyl)-4-methylcarbanilic                                                             4       4                                              acid-(3-(methylthio-carbonylamino)-phenyl)-                                    ester                                                                          N--(2,2-dimethoxyethyl)-3-methylcarbanilic                                                             4       4                                              acid-(3-methylthiocarbonylamino)-phenyl)-                                      ester                                                                          N--(2,2-dimethyoxyethyl)-3-methylcarbanilic                                                            4       4                                              acid-(3-(ethylthiocarbonylamino)-phenyl)-                                      ester                                                                          N--(2,2-dimethoxyethyl)-4-methylcarbanilic                                                             4       4                                              acid-(3-(ethylthiocarbonylamino)-phenyl)-                                      ester                                                                          N--(2-ethoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(methylthio-carbonylamino)-phenyl)-                                         ester                                                                          N--(2-methoxyethyl)-4-methylcarbanilic                                                                 4       4                                              acid-(3-(methylthiocarbonylamino)-phenyl)-                                     ester                                                                          N--(2-butoxyethyl)-4-methylcarbanilic                                                                  4       4                                              acid-(3-(methylthio-carbonylamino)-phenyl)-                                    ester                                                                          N--(2-ethoxyethyl)-2-methylcarbanilic acid-                                                            4       4                                              (3-(methylthio-carbonylamino)-phenyl)-ester                                    N--(2-methoxyethyl)-3-methoxycarbanilic                                                                4       4                                              acid-(3-(methylthio-carbonylamino)-phenyl)-                                    ester                                                                          N--(2-butoxyethyl)-carbanilic acid-(3-methyl-                                                          4       4                                              thiocarbonylamino)-phenyl)-ester                                               N--(2-methoxyethyl)-4-methoxycarbanilic acid-                                                          3       3                                              (3-(ethylthiocarbonylamino)-phenyl)-ester                                      N--(2-methoxyethyl)-4-methoxycarbanilic acid-                                                          4       4                                              (3-(1-methylethoxycarbonylamino)-phenyl)-                                      ester                                                                          N--(2-ethoxyethyl)-carbanilic acid-(3-(methyl-                                                         4       4                                              thio-carbonylamino)-phenyl)-ester                                              N--(2-methoxyethyl)-4-methoxycarbanilic                                                                4       4                                              acid-(3-(2-propinyloxycarbonylamino)-                                          phenyl)-ester                                                                  N--(2-methoyethyl)-4-methoxycarbanilic acid-                                                           4       4                                              (3-(1-methylpropoxycarbonylamino)-phenyl)-                                     ester                                                                          N--(2-methoxyethyl)-4-methoxycarbanilic                                                                4       4                                              acid-(3-(2-methylpropoxycarbonylamino)-                                        phenyl)-ester                                                                  N--(2-methoxyethyl)-3-methylcarbanilic                                                                 3       3                                              acid-(3-(ethylthiocarbonylamino)-phenyl)-                                      ester                                                                          N--(2-methoxyethyl)-3-methylcarbanilic acid-                                                           4       4                                              (3-(2-methylpropoxycarbonylamino)-phenyl)-                                     ester                                                                          N--(2-ethoxyethyl)-carbanilic acid-(3-(2-                                                              4       4                                              methylpropoxycarbonylamino)-phenyl)-ester                                      N--(2-ethoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(2-methylpropoxycarbonylamino)-phenyl)-                                     ester                                                                          N--(2-ethoxyethyl)-carbanilic acid-(3-(1-                                                              4       4                                              methylpropoxycarbonylamino)-phenyl)-ester                                      N--(2-methoxyethyl)-carbanilic acid-(3-(1-                                                             2       2                                              methyl-2-chloroethoxycarbonylamino)-phenyl)-                                   ester                                                                          N--(2,2-dimethoxyethyl)-carbanilic acid-(3-                                                            2       2                                              (1-methyl-2-chloroethoxycarbonylamino)-                                        phenyl)-ester                                                                  N--(2-methoxyethyl)-4-methoxycarbanilic                                                                4       4                                              acid-(3-(methylthiocarbonylamino)-phenyl)-                                     ester                                                                          N--(2,2-dimethoxyethyl)-carbanilic acid-(3-                                                            3       2                                              (2-bromoethoxycarbonylamino)-phenyl)-ester                                     N--(2,2-dimethoxyethyl)-carbanilic acid-                                                               4       4                                              (3-(2-methoxyethoxycarbonylamino)-phenyl)-                                     ester                                                                          N--(2-methoxyethyl)-2-methylcarbanilic acid-                                                           4       4                                              (3-(methylthiocarbonylamino)-phenyl)-ester                                     3-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(2-methylpropoxycarbonylamino)-phenyl)-                                     ester                                                                          N--(2-methoxyethyl)-4-methylcarbanilic acid-                                                           4       4                                              (3-(2-methylpropoxycarbonylamino)-phenyl)-                                     ester                                                                          N--(2-methoxyethyl)-3-methylcarbanilic acid-                                                           4       4                                              (3-(1-methylpropoxycarbonylamino)-phenyl)-                                     ester                                                                          3-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-methylthiocarbonylamino)-phenyl)-ester                                      N--(2-ethoxyethyl)-carbanilic acid-(3-                                                                 4       4                                              (allyloxycarbonylamino)-phenyl)-ester                                          N--(2-ethoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(allyloxycarbonylamino)-phenyl)-ester                                       N--(2-propoxyethyl)-carbanilic acid-(3-                                                                4       4                                              (allyloxycarbonylamino)-phenyl)-ester                                          N--(methoxyethyl)-carbanilic acid-(3-(2-                                                               --      --                                             bromoethoxycarbonylamino)-phenyl)-ester                                        N--(2-butoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(methoxycarbonylamino)-phenyl)-ester                                        N--(2-butoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(ethoxycarbonylamino)-phenyl)-ester                                         N--(2,2-diethoxyethyl)-carbanilic acid-(3-                                                             4       4                                              (ethoxycarbonylamino)-phenyl)-ester                                            N--(2-propoxyethyl)-carbanilic acid-(3-(1-                                                             4       4                                              methylethoxycarbonylamino)-phenyl)-ester                                       N--(2-butoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(1-methylethoxycarbonylamino)-phenyl)-                                      ester                                                                          3-methyl-N--(2-propoxyethyl)-carbanilic                                                                4       4                                              acid-(3-(1-methylethoxycarbonylamino)-                                         phenyl)-ester                                                                  N--(2-butoxyethyl)-4-methylcarbanilic                                                                  4       4                                              acid-(3-(1-methylethoxycarbonylamino)-                                         phenyl)-ester                                                                  N--(2-butoxyethyl)-carbanilic acid-(3-                                                                 4       4                                              (1-methylethoxycarbonylamino)-phenyl)-                                         ester                                                                          N--(2,2-diethoxyethyl)-carbanilic acid-                                                                4       4                                              (3-(allyloxycarbonylamino)-phenyl)-                                            ester                                                                          N--(2-methoxyethyl)-2-methylcarbanilic                                                                 4       4                                              acid-(3-(2-propenyloxycarbonylamino)-                                          phenyl)-ester                                                                  N--(2,2-diethoxyethyl)-carbanilic acid-                                                                4       4                                              (3-(2-methylpropoxycarbonylamino)-                                             phenyl)-ester                                                                  N--(2,2-diethoxyethyl)-carbanilic acid-                                                                4       4                                              (3-(2-propinyloxycarbonylamino)-phenyl-                                        ester                                                                          N--(2-ethoxyethyl)-4-methylcarbanilic acid-                                                            4       4                                              (3-(methylthiocarbonylamino)-phenyl)-ester                                     N--(2,2-diethoxyethyl)-carbanilic acid-(3-                                                             4       4                                              (methylthio-carbonylamino)-phenyl)-ester                                       4-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(methylthio-carbonylamino)-phenyl)-ester                                    2-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(methylthio-carbonylamino)-phenyl)-ester                                    N--(2-butoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(methylthio-carbonylamino)-phenyl)-ester                                    N--(2-propoxyethyl)-carbanilic acid-(3-                                                                4       4                                              (ethylthio-carbonylamino)-phenyl)-ester                                        3-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(ethylthio-carbonylamino)-phenyl)-ester                                     N--(2-butoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(ethylthio-carbonylamino)-phenyl)-ester                                     N--(2-butoxyethyl)-4-methylcarbanilic acid-                                                            4       4                                              (3-ethylthio-carbonylamino)-phenyl)-ester                                      N--(2-cyanoethyl)-3-chlorocarbanilic acid-                                                             4       4                                              (3-(allyloxycarbonylamino)-phenyl)-ester                                       3-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(2-propinyloxycarbonylamino)-phenyl)-ester                                  N--(2-propoxyethyl)-carbanilic acid-(3-(2-                                                             4       4                                              propinyloxycarbonylamino)-phenyl)-ester                                        N--(2-butoxyethyl)-4-methylcarbanilic acid-                                                            4       4                                              (3-(2-propinyloxycarbonylamino)-phenyl)-                                       ester                                                                          N--(2-butoxyethyl)-carbanilic acid-(3-(2-                                                              4       4                                              propinyloxycarbonylamino)-phenyl)-ester                                        2-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(2-propinyloxycarbonylamino)-phenyl)-ester                                  N--(2-butoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(2-propinyloxycarbonylamino)-phenyl)-                                       ester                                                                          4-methyl-N-- 13 (2-propoxyethyl)-carbanilic acid-                                                      4       4                                              (3-(2-propinyloxycarbonylamino)-phenyl)-ester                                  N--(2-ethoxyethyl)-carbanilic acid-(3-(ethyl-                                                          4       4                                              thiocarbonylamino)-phenyl)-ester                                               N--(2-ethoxyethyl)-3-methylcarbanilic acid-                                                            4       4                                              (3-(ethylthiocarbonylamino)-phenyl)-ester                                      2-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(ethylthiocarbonylamino)-phenyl)-ester                                      N--(2-ethoxyethyl)-4-methylcarbanilic acid-                                                            4       4                                              (3-(ethylthiocarbonylamino)-phenyl)-ester                                      4-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(ethylthiocarbonylamino)-phenyl)-ester                                      N--(2-methoxyethyl)-4-methylcarbanilic acid-                                                           4       4                                              (3-ethylthiocarbonylamino)-phenyl)-ester                                       N--(2-ethoxyethyl)-2-methylcarbanilic acid-                                                            4       4                                              (3-(ethylthiocarbonylamino)-phenyl)-ester                                      N--(2-methoxyethyl)-3-methoxycarbanilic acid-                                                          4       4                                              (3-ethylthio-carbonylamino)-phenyl)-ester                                      N--(2-methoxyethyl)-3-methylcarbanilic acid-                                                           4       4                                              (3-(methylthio-carbonylamino)-phenyl)-ester                                    2-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(ethoxycarbonylamino)-phenyl)-ester                                         N--(2-ethoxyethyl)-carbanilic acid-(3-(1-                                                              4       4                                              methylethoxycarbonylamino)-phenyl)-ester                                       N--(2-methoxyethyl)-4-methylcarbanilic acid-                                                           4       4                                              (3-(1-methylethoxycarbonylamino)-phenyl)-                                      ester                                                                          N--(2-ethoxyethyl)-4-methylcarbanilic acid-                                                            4       4                                              (3-(1-methylethoxycarbonylamino)-phenyl)-                                      ester                                                                          1-methyl-N--(2-propoxyethyl)-carbanilic acid-                                                          4       4                                              (3-(1-methylethoxycarbonylamino)-phenyl)-                                      ester                                                                          4-methyl-N--(2-propoxyethyl)-carbanilic                                                                4       4                                              acid-(3-(1-methylethoxycarbonylamino)-                                         phenyl)-ester                                                                  4-methyl-N--(2-propoxyethyl)-carbanilic                                                                4       4                                              acid-(3-(ethoxycarbonylamino)-phenyl)-                                         ester                                                                          N--(2-ethoxyethyl)-3-methylcarbanilic                                                                  4       4                                              acid-(3-(1-methylethoxycarbonylamino)-                                         phenyl)-ester                                                                  N--(2-ethoxyethyl)-2-methylcarbanilic acid-                                                            4       4                                              (3-(1-methylethoxycarbonylamino)-phenyl)-                                      ester                                                                          ______________________________________                                    

EXAMPLE 3

The compounds listed below in Table II and identified by the numbers of the above list of compounds were applied in a hothouse in a postemergence application to the plants likewise listed in the table. The amounts were 1 kg of active agent per about 2.5 acres. The comparison compound in the tests was 3-methylcarbanilic acid-(3-(methoxycarbonylamino)-phenyl)-ester.

The plants were in the growing stage. The applied amount of liquid corresponded about to 500 liter per 2.5 acres. The agents were applied in the form of emulsions.

The results were evaluated after 14 days on a scale of 10=no damage to the plants to 0=total destruction of the plants.

As appears from the table with the compounds of the invention there resulted a good compatibility for agricultural plants together with a high activity against weeds. The composition compound on the other hand caused substantial damage to the agricultural plants at a lower weed activity.

                                      TABLE II                                     __________________________________________________________________________     Compound of the                                                                          pota-                   Valeria-                                     Invention No.                                                                            toes                                                                               cotton                                                                             peanuts                                                                            rice                                                                              carrots                                                                            Digitalis                                                                           nella                                                                               Trifolium                                                                           Portulaca                                                                           Papaver                                                                             Kochia                                                                             Solanum              __________________________________________________________________________      2.       10  10  10  10 10  0    0    0    0    0    0   0                    15.       10  10  10  10 10  0    0    0    0    0    0   0                    37.       10  10  10  10 10  0    0    0    0    0    0   0                    Comparison                                                                     compound                                                                       3-Methylcarbanilic                                                                       5   2   7   4  2   2    0    1    0    1    2   3                    acid -(3-(methoxy-                                                             carbenylamino)-                                                                phenyl)-ester                                                                  Untreated 10  10  10  10 10  10   10   10   10   10   10  10                   __________________________________________________________________________     Compound of the                                                                          Escholt-                                                                            Euphor-                               Echino-                   Invention No.                                                                            zia  bia  Brassica                                                                            Datura                                                                             Ipomea                                                                             Setaria                                                                            Agrostis                                                                            Alopecurus                                                                           Bromus                                                                              chloa                                                                               Digitaria            __________________________________________________________________________      2.       0    0    0    0   0   0   0    0     0    0    0                    15.       0    0    0    0   0   0   0    0     0    0    0                    37.       0    0    0    0   0   0   0    0     0    0    0                    Comparison                                                                     compound                                                                       3-Methylcarbanilic                                                                       1    3    0    0   0   3   5    7     6    10   8                    acid -(3-(methoxy-                                                             carbenylamino)-                                                                phenyl)-ester                                                                  Untreated 10   10   10   10  10  10  10   10    10   10   10                   __________________________________________________________________________

Without further analysis, the foregoing will so fully reveal the gist of the present invention that others can, by applying current knowledge, readily adapt it for various applications without omitting features that, from the standpoint of prior art, fairly constitute essential characteristics of the generic or specific aspect of this invention. 

What is claimed as new and desired to be protected by Letters Patent is set forth in the appended claims:
 1. Diurethane of the formula ##STR9## N-(2-Methoxyethyl)-carbanilic acid-(3-methoxy carbonylamino)-phenyl-ester, wherein R=CH₃, X=O, R₁ =2-methoxyethyl and n=o.
 2. Diurethane of the formula ##STR10## N-(2,2-Dimethoxyethyl)-carbanilic acid-(3-methylthiocarbonylamino)-phenyl-ester, wherein R=CH₃, X=S, R₁ =2,2-dimethoxy ethyl and n=o.
 3. Diurethane of the formula ##STR11## N-(2-Methoxyethyl)-carbanilic acid-(3-methylthiocarbonylamino)-phenyl-ester, wherein R=CH₃, X=S, R₁ =2-methoxyethyl and n=o.
 4. A herbicidal composition comprising from about 10 to 80% by weight of at least one diurethane selected from the group consisting of N-(2-Methoxyethyl)-carbanilic acid-(3-methoxy carbonylamino)-phenyl-ester,N-(2,2-Dimethoxyethyl)-carbanilic acid-(3-methylthiocarbonylamino)-phenyl-ester, and N-(2-Methoxyethyl)-carbanilic acid-(3-methylthiocarbonylamino)-phenyl-ester, and about 90 to 20% by weight of a liquid or solid inert carrier material with or without up to 20% by weight of a surface active agent upon corresponding reduction of the amount of carrier material. 